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Check back for information about the 2016 match-up at Tampa Prep!

History of the Headmasters' Challenge
Remembering the intense rivalry between Deerfield Academy (where Tampa Prep’s Former Headmaster, Gordon MacLeod, taught) and Choate (where Berkeley’s Headmaster Joseph Merluzzi taught), Mr. MacLeod suggested that a similar day be developed between Tampa Prep and Berkeley. Mr. Merluzzi readily agreed, acknowledging the fun and good competition that resulted from the Deerfield-Choate day and the possibility for Tampa Prep and Berkeley to have the same experience. The prize the schools would compete for was the Headmasters Cup, which would reside at the winning school for the year.

Tampa Prep hosted the inaugural Headmasters' Challenge on January 10, 2004. The competition featured 15 winter sports from middle division, junior varsity and varsity.

Headmasters' Challenge Results

2004 @Tampa Prep (Winner: Berkeley Prep Score:12-7)

2005 @Berkeley Prep (Winner: Berkeley Prep Score: 11.5-8.5)

2006 @Tampa Prep (Winner: Tampa Prep Score: 15.5-4.5)

2007 @Berkeley Prep (Winner: Tampa Prep Score: 10.5-9.5)

2008 @Tampa Prep (Winner: Berkeley Prep Score: 12-9)

2009 @Berkeley Prep (Winner: Berkeley Prep Score: 17.5-3.5)

2010 @Tampa Prep (Winner: Berkeley Prep Score: 12-7)

2011 @ Berkeley Prep (Winner: Tampa Prep Score 10.5-9.5)

2012 @ Tampa Prep (Winner: Tampa Prep Score 13.5-6.5)

2013 @ Berkeley Prep (Winner: Berkeley Prep 12-10)

2014 @ Tampa Prep (Tied 9.5-9.5)

2015 @ Berkeley Prep (Winner: Berkeley Prep 13-6)

More than just a college preparatory school...a preparation for life with a higher purpose than self

  • Tampa Preparatory School
  • Grades 6-12
  • tel 813 251 8481
  • 727 West Cass St, Tampa, FL, 33606
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